#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:33:47 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179146 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/07/4310704.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4310704
loop_
_publ_author_name
'Dongbin Zhao'
'Zhaofu Fei'
'Rosario Scopelliti'
'Paul J. Dyson'
_publ_contact_author_address
;
Institut de Chimie Moléculaire et Biologique
École Polytechnique Fédérale de Lausanne
1015 Lausanne
Switzerland
;
_publ_contact_author_email       paul.dyson@epfl.ch
_publ_contact_author_fax         '+41 21 693 9885'
_publ_contact_author_name        'Paul J. Dyson'
_publ_contact_author_phone       '+41 21 693 9854'
_publ_section_title
;
 Synthesis and Characterization of Ionic Liquids Incorporating the Nitrile
 Functionality
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2197
_journal_page_last               2205
_journal_paper_doi               10.1021/ic034801p
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C8 H12 F6 N3 P'
_chemical_formula_weight         295.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.12(3)
_cell_angle_beta                 87.01(3)
_cell_angle_gamma                74.95(5)
_cell_formula_units_Z            2
_cell_length_a                   8.022(4)
_cell_length_b                   8.161(5)
_cell_length_c                   9.460(2)
_cell_measurement_reflns_used    1021
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      21.50785
_cell_measurement_theta_min      2.10285
_cell_volume                     597.1(5)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'marresearch mar345'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'marresearch mar345 IPDS'
_diffrn_measurement_method
'60 images with deltaphi = 3 deg. and exp. time = 180 sec.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3890
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.6330
_exptl_absorpt_correction_T_min  0.1600
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
; 
(See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.029(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1183P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1794
_reflns_number_gt                1362
_reflns_number_total             1985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034801psi20030710_030258_4.cif
_cod_data_source_block           3b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4310704
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.37058(11) 0.27699(11) 0.31727(9) 0.0446(4) Uani 1 1 d . . .
F1 F 0.1995(3) 0.4246(3) 0.3542(2) 0.0575(6) Uani 1 1 d . . .
F2 F 0.4194(3) 0.3932(3) 0.1902(2) 0.0565(6) Uani 1 1 d . . .
F3 F 0.2652(3) 0.1965(3) 0.2121(2) 0.0569(6) Uani 1 1 d . . .
F4 F 0.5414(3) 0.1307(3) 0.2805(2) 0.0560(6) Uani 1 1 d . . .
F5 F 0.3210(3) 0.1633(3) 0.4454(2) 0.0612(6) Uani 1 1 d . . .
F6 F 0.4748(3) 0.3591(3) 0.4228(2) 0.0541(6) Uani 1 1 d . . .
N1 N 0.8531(4) 0.3301(4) 0.2914(3) 0.0473(7) Uani 1 1 d . . .
N2 N 0.7690(3) 0.5705(4) 0.1794(3) 0.0465(7) Uani 1 1 d . . .
N3 N 0.0715(4) 0.8496(4) 0.1922(4) 0.0612(9) Uani 1 1 d . . .
C1 C 0.8656(4) 0.2946(5) 0.1493(4) 0.0499(8) Uani 1 1 d . . .
H1 H 0.9039 0.1855 0.1088 0.060 Uiso 1 1 calc R . .
C2 C 0.8134(4) 0.4442(5) 0.0786(3) 0.0477(8) Uani 1 1 d . . .
H2 H 0.8079 0.4601 -0.0212 0.057 Uiso 1 1 calc R . .
C3 C 0.7951(4) 0.4962(5) 0.3052(4) 0.0490(8) Uani 1 1 d . . .
H3 H 0.7752 0.5534 0.3928 0.059 Uiso 1 1 calc R . .
C4 C 0.8954(5) 0.2043(5) 0.4076(4) 0.0570(9) Uani 1 1 d . . .
H4A H 0.8906 0.2629 0.4970 0.085 Uiso 1 1 calc R . .
H4B H 1.0119 0.1308 0.3898 0.085 Uiso 1 1 calc R . .
H4C H 0.8118 0.1352 0.4133 0.085 Uiso 1 1 calc R . .
C5 C 0.6981(5) 0.7527(5) 0.1507(4) 0.0508(9) Uani 1 1 d . . .
H5A H 0.7613 0.7880 0.0674 0.061 Uiso 1 1 calc R . .
H5B H 0.7154 0.8176 0.2329 0.061 Uiso 1 1 calc R . .
C6 C 0.5064(4) 0.7941(5) 0.1228(4) 0.0477(8) Uani 1 1 d . . .
H6A H 0.4877 0.7157 0.0511 0.057 Uiso 1 1 calc R . .
H6B H 0.4696 0.9110 0.0830 0.057 Uiso 1 1 calc R . .
C7 C 0.3937(4) 0.7799(4) 0.2566(3) 0.0463(8) Uani 1 1 d . . .
H7A H 0.4301 0.6635 0.2975 0.056 Uiso 1 1 calc R . .
H7B H 0.4094 0.8600 0.3281 0.056 Uiso 1 1 calc R . .
C8 C 0.2120(5) 0.8186(4) 0.2226(3) 0.0484(8) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F4 P1 F3 90.20(12) . . ?
F4 P1 F5 90.21(13) . . ?
F3 P1 F5 90.38(12) . . ?
F4 P1 F6 90.29(12) . . ?
F3 P1 F6 179.50(12) . . ?
F5 P1 F6 89.72(12) . . ?
F4 P1 F2 90.38(13) . . ?
F3 P1 F2 90.11(12) . . ?
F5 P1 F2 179.23(12) . . ?
F6 P1 F2 89.79(12) . . ?
F4 P1 F1 179.71(12) . . ?
F3 P1 F1 90.00(12) . . ?
F5 P1 F1 89.99(13) . . ?
F6 P1 F1 89.51(12) . . ?
F2 P1 F1 89.42(13) . . ?
C3 N1 C1 108.3(3) . . ?
C3 N1 C4 126.0(3) . . ?
C1 N1 C4 125.7(3) . . ?
C3 N2 C2 107.6(3) . . ?
C3 N2 C5 126.3(3) . . ?
C2 N2 C5 126.0(3) . . ?
C2 C1 N1 107.1(3) . . ?
C2 C1 H1 126.5 . . ?
N1 C1 H1 126.5 . . ?
C1 C2 N2 107.1(3) . . ?
C1 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
N2 C3 N1 109.9(3) . . ?
N2 C3 H3 125.1 . . ?
N1 C3 H3 125.1 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 111.5(3) . . ?
N2 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 112.9(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 110.3(3) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N3 C8 C7 178.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F4 1.597(2) . ?
P1 F3 1.598(2) . ?
P1 F5 1.599(2) . ?
P1 F6 1.602(2) . ?
P1 F2 1.602(2) . ?
P1 F1 1.605(2) . ?
N1 C3 1.322(5) . ?
N1 C1 1.377(4) . ?
N1 C4 1.470(4) . ?
N2 C3 1.320(4) . ?
N2 C2 1.392(5) . ?
N2 C5 1.469(5) . ?
N3 C8 1.139(5) . ?
C1 C2 1.350(5) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.522(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.536(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.460(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -0.1(4) . . . . ?
C4 N1 C1 C2 179.4(3) . . . . ?
N1 C1 C2 N2 0.0(4) . . . . ?
C3 N2 C2 C1 0.1(4) . . . . ?
C5 N2 C2 C1 -177.2(3) . . . . ?
C2 N2 C3 N1 -0.1(4) . . . . ?
C5 N2 C3 N1 177.2(3) . . . . ?
C1 N1 C3 N2 0.1(4) . . . . ?
C4 N1 C3 N2 -179.3(3) . . . . ?
C3 N2 C5 C6 -98.6(4) . . . . ?
C2 N2 C5 C6 78.2(4) . . . . ?
N2 C5 C6 C7 71.4(4) . . . . ?
C5 C6 C7 C8 -179.1(3) . . . . ?
C6 C7 C8 N3 -2(12) . . . . ?
